


Taking Chances

by ByTheDawn



Series: Stolen Moments [5]
Category: Once Upon a Time (TV)
Genre: Alternate Universe, Alternate Universe - Canon Divergence, F/F, First Date, First Kiss
Language: English
Status: Completed
Published: 2014-01-05
Updated: 2014-01-05
Packaged: 2018-01-07 13:28:44
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,019
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1120390
Author URL: https://archiveofourown.org/users/ByTheDawn/pseuds/ByTheDawn
Summary: <blockquote class="userstuff">
              <p>Written for the <a href="http://swanqueenweek.tumblr.com/">Swan Queen Week Midwinter 2014</a>. Day one: AU Blind Date.</p><p>Henry presses his mom to accept a date with a woman he knows from school, why? Because it's time she got over his dad and Miss Swan is perfect for her--he just knows it.</p>
            </blockquote>





	Taking Chances

**Author's Note:**

> “Mom, come _on_! It’s been years since you’ve been on a date, and I know you will always love dad—me too—but he’s been dead for years. So why not? She’s perfect for you, I promise. You’ll like her.”

Regina Mills pinched the bridge of her nose at her sixteen-year-old’s incessant prodding. For weeks now, he had been pushing her to accept this insane idea of a date with a random woman who worked at his high school. For weeks now, Regina had been shooting the idea down without a second thought, but she had to admit, he was starting to wear her down.

“Henry, for the last time, I am not going on a date with one of your teachers.” She answered him dismissively and in a tone which—what she hoped—would put an end to this discussion once and for all. She could tell by the way her son’s eyes lit up, though, that she had at least failed in the latter category.

“Miss Swan is not a teacher, she is head of security at the fancy hell you have me attend five days a week, so don’t make this about her pay check or her social standing. She’s a little younger than you, but, you know, that should just be flattering, and I still have very vivid memories that make me believe the chick thing is not an issue, so… what is?” Henry pushed. Finally distracted enough to put the papers she’d been trying to read down on her desk, she fully turned to her son, who had slouched himself down onto one of the visitor chairs opposite her in her home office. It was too late in the day for this.

“Henry, let me be very clear. If you ever refer to a woman as a ‘chick’ again, you will be grounded for a month. I mean it. As for Miss Swan, I am sure she is a wonderful person, and I have no doubt you find her perfectly pleasing to the eye, but I have neither the time nor the need for a partner in my life.” Her voice was beautifully motherly, and Regina mentally patted herself on the back for a job well done. Henry rolled his eyes.

“Sorry, mom.” He said, and he had the decency to actually sound sorry. 

“Why would you even assume she would agree to a date with a woman?” Regina asked, unable to keep herself from satisfying her one curiosity about the woman her son was pushing on her. Henry’s eyes lit up dangerously and she sighed. She should not have said anything. She should just have lived with not knowing. She could read her son like an open book, and right now, his face read—in size 42, bold—that he had renewed hope. Damn it, Regina. Henry sat up straight in his chair, and she barely contained a snort. Well, if only she had known earlier getting her son to display proper manners was tied to her willingness to date a complete stranger.

“Because I asked her.”

Regina’s eyes went wide.

“You did what?!” She requested incredulously. 

“I asked her. It was a bit of a dare but she hangs out with some of us sometimes, so it wasn’t that weird. She simply said that ‘she was open to new experiences’, and so we took that as a yes.” He answered her simply, making air quotes around Miss Swan’s comment. Regina set her lips in a tight line.

“You were out of line in asking her that, and she was out of line in even answering—let alone with such vagueness.” She answered, her mind quickly judging the woman and finding her lacking. No matter that she was employed by the top private school in the greater New York area, and no matter that her son liked her, she was not doing it. Sighing, she reached for her files again.

“Henry, I am not agreeing to a date with your… friend. Now, I have work to do, so if you would please excuse me? Oh—before you go, would you mind leaving your Monday afternoon free? I will book you an appointment with the hairdresser. This insanity of growing out your hair is coming to an end.” She said it casually, but she could see by Henry’s shocked and hurt expression that she was in for a world of hurt. She had known she would be, but it really would not do to have him—the son of one of New York’s most powerful judges—walking around like he was in one of those ridiculous boy bands.

“What?! No! No way! I am not cutting my hair. No way in hell, and you can’t make me!” He shouted at her as he jumped up, one hand defensively planting itself on his head. Regina took a steadying breath, put down the papers again, and folded her hands.

“I am your mother, Henry, and until you are eighteen years old, I am responsible for your well-being, and that includes your appearance. You will be getting your hair cut on Monday and that is final.” She spoke in the tone of voice that had many lawyers quake in their overpriced shoes.

“No.” Henry said simply, spitting out the word.

“I am not debating this with you, Henry.” Regina answered tiredly. “My word is final.” She said and watched Henry’s face go from denial, to anger, to the third stage of grief: bargaining.

“Okay,” he said, planting his hands on the desk and looking her square in the eye—well, she could see one of his eyes, the other was hidden by his God awful do. She leaned back to await his offer. She knew she could drag him through all five stages of grief before Monday, but she would prefer not having to. If this was going to cost her another gaming console then so be it.

“How about this: if you agree to go on a date with Miss Swan this Saturday and you hate it, I will get my hair cut on Monday without even moaning about it. I will go to the hairdressers as meek as a lamb; no shouting, no nothing.” He looked at her with a challenge in his eyes, and she regarded him curiously. If this date thing was important enough for him to cut of his beloved hair, then something must really be up with it.

“Why is this so important to you, sweetheart?” She asked, postponing answering his proposal. He huffed and stood, breaking eye contact with her.

“Because, mom… I may have been young when dad died, but I saw how it hurt you. You were never the same after that and… I just want you to be happy. I think Miss Swan could make you happy.” That was twice in a day Henry had brought up Daniel, and she couldn’t say it did not bring back painful memories. Henry had been so little when Daniel had been murdered, but yes, she supposed he would have seen what it did to her. It had not changed her for the better, that was for sure. 

“Alright.” She finally said. Henry’s eyes bulged.

“Wait, what? You’re saying yes? To the date?” He asked, obviously wanting to check if he had gotten this right—after so many weeks of all out being shot down, Regina was now agreeing?

“I am saying yes,” She corrected quickly, “…to your proposal: I go on a date and if I hate it, you will get your hair cut on Monday.”

“Okay… but we need to establish what defines ‘hate’.” Henry said, and Regina hid a smirk. That was her boy. As she watched Henry sit down, she leaned back with a nod.

“Alright, that is fair. Perhaps, though, we should define a successful date instead?” She offered, and he thought over her words carefully, looking for loopholes in this change of definition. He nodded.

“Okay, I am pretty confident that this will work out, so here goes: if you two kiss, I get to keep my hair.” Henry said, a smirk on his beautiful face. Regina laughed—she tried to suppress it, but his comment took her by surprise so much, she couldn’t. 

“Who says I let anyone kiss me on the first date?” She asked with a smirk of her own. 

“You will let Miss Swan kiss you. I just know it.” 

Regina shook her head. He really had a high opinion of the woman. Still, this was just about the safest bet she could ever make. 

“Alright, I agree to your terms. If you arrange a date Saturday with Miss Swan, I will dress my best, be my best, and give it a fair chance. If we kiss by the end of it, you get to keep your hair, if not, you are going to the hairdressers on Monday.” She summarized and he nodded. Leaning forward, he extended his hand for her to shake—which she did.

“Deal.”

“Deal.”

 

By the next day, Regina had all but forgotten the strange conversation with her son—no, that was not true. It was swirling somewhere deep inside of her, a buzzing that would not go away and it had plagued her since the moment she had said ‘yes’. There was an image in her head of a faceless blonde woman, leaning in to press her lips gently against hers, and the thought alone was so distracting that she pushed it away every single time it surfaced. She had come in to work today, as she had to preside over the one trial on her docket today, but she was very tempted to go home now it was settled. Henry should be home soon, and it had been a while since she had spent any time with him that was not a typical family affairs like breakfast, dinner, and car rides to school or an activity.

Her phone ringing startled her, and she noticed it was her private one. Henry’s picture showed up—one in which his hair was blissfully short—and she answered it on speaker phone.

“Henry, what can I do for you?” She asked pleasantly. He rarely—if ever—called her at work, so this was either and emergency, or something about her date. Her stomach rolled with the thought it was likely the latter.

“It’s all set up, dinner at seven at Marea. I used your name to get the reservation. She will be wearing a red dress. She’s blonde, by the way. Enjoy!” Henry sounded positively joyful, but he did not let her ask any questions; instead she was met by the quietness of a disconnected call.

Regina leaned back with a surprised expression on her face. She had not expected her son would go through with this idea, she had not expected Miss Swan to say ‘yes’, and she certainly had not expected the woman to be available tomorrow evening, on a Saturday, for an impromptu blind date. The fact that she was actually going on this date was enough to make her smile in the privacy of her office, however, and she allowed herself to. Perhaps it was time to finally let a little bit of happiness back into her life… and if Henry had faith in this woman, then maybe so could she.

 

Seven PM on Saturday rolled along far quicker then Regina had expected and as stood in the lobby of the beautiful Italian restaurant, she had to take a moment to swallow down her nerves. She was a grown woman, damn it, and it was just a date. Just a date, with someone she did not know and had no obligation to like or entertain. She was here to please her son, nothing more. She could do this. And yet, she found herself looking over her tight black dress, making sure her cleavage was impressive enough, and that she didn’t have a run in her tights. She didn’t and she looked exquisite, if she did say so herself. Alright, she was going in. It took her a few more seconds to get her feet—stuck in uncomfortable high heeled shoes—to move forward, and she clutched her bag a tad too tightly for her own liking. Sighing at her own willingness to get hurt, she stepped through the heavy door and into the buzz of dining New Yorkers.

“Good evening, welcome to Marea. May I take your name?” 

The young waiter a little over Henry’s age smiled pleasantly at her and nodded when she gave him her family name. He tapped the screen in front of him and stepped out from behind the station to accompany her to a table near the back. Regina was pleasantly surprised to see a figure in a red dress already seated at the table. Her face was hidden by beautiful and luscious blonde hair that tumbled in curls over her shoulder. Very little of the blonde’s figure was hidden by her chair, and Regina has to shallowly admit that the woman’s physique was more then pleasing. She swallowed heavily and stopped the slight tremor in her hand. 

She was not nervous, and if she continued to tell herself, she would start to believe it soon enough. Still, she managed to mould her face into something she hoped at least resembled calm collectiveness, and smiled when the man’s voice announcing her arrival at the table drew the woman out of her reverie. As soon as Regina’s eyes landed on her date’s face, the dark haired woman froze.

She was beautiful. Not just pretty in the typical sense of the word, but truly _beautiful_. The waves of soft curls framing a flawless face, her sparkling green eyes which regarded her with a hint of shyness but which were offset by a cocky smirk on full lips… Henry was right, she was perfect—if she could carry a conversation, of course.

The waiter faded in the crowd as Emma stood and extended her hand. Regina took it, and marvelled at the way her pulse jumped at the simple touch. 

“Hi, I’m Emma. Thank you for agreeing to meet with me. I have heard a lot about you.” The blonde said and Regina found herself blushing.

“All good, I hope? I’m Regina, and the pleasure is all mine.” She assured, slowly—regrettably—letting go of the hand in hers after Emma nodded to confirm that, yes, it everything she had heard had been all good. They stood a moment and then Emma moved in front of her, pulling the chair opposite the one she had just been occupying out and letting Regina take her place in it before pushing lightly.

“Thank you.” Regina said, feeling particularly wooed by the gesture. Emma shrugged as she took her place.

“I can be smooth when the right woman comes along.” Emma spoke, and Regina smiled despite herself. 

“Getting a little ahead of ourselves, aren’t we?” She answered, happy to find her sass returning to her after the impromptu vacation it seemed to have taken in the face of Miss Emma Swan. Emma stared at her for a moment, meeting her eyes without hesitation.

“We’ll see.” She eventually answered with a smile. Regina swallowed heavily, and she could see by the light twitch at the corner of Emma’s mouth that Emma had caught her. Regina thought she would have minded being found out but she didn’t. Instead, she smiled and reached for her napkin, folding it neatly over her lap. 

“How about we order something to eat?” She suggested and Emma’s eyes finally released her.

“That sounds like a plan.”

. 

The evening went by too fast, Regina decided. She had taken a cab to the restaurant, and Emma had wordlessly invited herself to drive Regina home by the end of what Regina could very easily label her most successful date ever. Emma was smart, funny, and she had a wicked side to her that gave Regina shivers whenever it manifested. The woman had a natural smoothness to her that was offset by her admitted love of comic books, stories of embarrassing spills and bumps, and a weakness for junk food. She also carried with her a deep sadness that she had only hinted at briefly. Like Regina, Emma had grown up mostly without family to fall back on, and it had been a connecting moment for the both of them to find that out, Regina was sure. As Emma walked her to the door, Regina felt her stomach jump and her pulse quicken. Although she hated what it would cost her, she was hoping Emma would, indeed, kiss her.

As they reached the porch, Regina turned and watched Emma climb the steps after her, eyes fluttering up to fall upon her own as Emma stepped a little too far into her personal space. Regina covered her nervousness with a rushed out ‘thank you’.

“I had a really good time tonight.” She admitted and Emma smiled brightly. Regina melted a little.

“Me too.” Emma confirmed and took another small step towards her as she searched her eyes for any sign of resistance. Emma licked her lips and Regina’s eyes followed the movement, lingering on her lips a moment too long before dragging them back up to marvellous green.

“Unless you have any objections, Judge Mills, I am going to kiss you now.” Emma whispered, a velvet darkness clinging to the words that made Regina’s breath hitch.

“No objections.” She assured quietly, her eyes falling back upon lips she had been thinking about kissing the moment she had first laid eyes on them. Emma licked them again and swallowed before closing even more of the distance between them and reaching out to gently pull Regina flush against her. Regina let herself be pulled in and marvelled at the hidden strength in slender arms—Emma would have to be strong, with her type of job, wouldn’t she?—and wrapped her arms around Emma’s neck lightly. Still, their lips had not met, still Emma was just searching her eyes with a gentle smile on her face, and Regina felt like she was about to explode with anticipation.

When Emma finally—finally—closed the minute gap between them, Regina was shocked to find herself moaning into the very innocent kiss. How did Emma do this to her? Musings of that variety would have to wait, however, because Emma’s lips were burning against her own and they were every bit as soft as she had imagined them to be. She pulled the woman a little tighter against her, cupping the back of her head with one hand as she parted her lips under Emma’s, inviting her to explore deeper even though Emma had not asked her for the privilege.

It took only a moment more before Emma’s warm tongue found hers in her mouth, and Regina was thrilled to find Emma moaning this time. The pressure against her lower back became a bit more forceful as the kiss deepened and Regina lost all sense of time and place as they slowly tasted each other. When Emma broke away with one, two, more kisses against her swollen lips, Regina was breathing heavily and smiling effortlessly. She hadn’t smiled this much in years, of that Regina was sure.

Emma slowly released her, and green eyes found her dark ones again. Emma licked her lips and grinned.

“Good night, Regina.” Emma said and turned to walk away, descending the stairs smoothly.

“Wait!” Regina found herself saying. Emma turned around. “Don’t you… would you like to come in?” she added—again, amazing herself. Emma just shook her head with a soft smile.

“Let’s save that for our next date.” Emma said and turned back around. This time, Regina watched her go, not feeling rejected in the least. In fact, she felt quite flattered and yes, again, quite wooed. She watched Emma get in her car—a perfectly restored 1982 yellow Volkswagen Beetle—and stood quietly by as she drove off with a last smile that Regina mirrored. Her lips still tingled in memory of that fairy tale kiss they had just shared.

By the time Regina got her faculties back, she realized she had been standing outside of her own home for a good few minutes now. Shaking her head with a smile, she fished her keys out of her clutch and opened the door. Henry’s voice startled her as she closed the door behind her. She spun around to find him half way up the staircase, watching her with amusement on his features.

“So?” He asked, and Regina chased the smile off of her features. She paused a moment, but realized she couldn’t say anything but the truth. With a sigh, she waved her free hand dismissively in his direction.

“You can keep your hair.” She admitted gruffly, and he jumped up.

“Yes! I told you!” He was downstairs in seconds, and before she knew it, he had picked her up and twirled her around before putting her back down. She couldn’t quite contain the undignified squeal that escaped her at the treatment. Still, her heart soared at his display of affection and she marvelled at his height. When, exactly, had he outgrown her? He stepped back a little, obviously a little embarrassed by his actions, but she could see the warmth belying his eyes as he looked at her.

“I’m happy for you, mom.” He said genuinely, and she smiled, reaching out to cup his cheek for a moment. He allowed her to, and her smile widened of its own accord. His hair seemed to be an afterthought to her happiness, and that touched her greatly. 

“Me too. Thank you.” She answered him with equal emotion and he nodded, turning around to head back upstairs. She watched him go, her little man, her eternal saviour—the truest believer in her. Her eyes remained on the staircase long after he was gone, but she did not mind. It had been quite the night, and she had a lot to process. That processing was put to a halt, however, when her phone pinged—her private one, the one only a hand full of people had the number to.

It was a text message, from Emma, whom she had given the number to on a whim. 

_’What are you doing for lunch tomorrow?’_

Regina found herself smiling again.

 _Presumptuous, aren’t we?’_ she wrote back. By the time she had hung up her coat, the phone pinged again.

_’We’ll see. The Corner Bistro, one PM.’_

Regina hesitated only a few moments before she quickly typed out her reply. Afterwards, she turned off the lights in the large house and locked the doors. Once she got back to her phone, she found the notification light blinking.

 _’I look forward to it’,_ the short message read, but it had Regina smiling brightly regardless. With a bounce in her step, she ascended the stairs and turned off the last of the lights. Gently, she rapped her knuckles on her son’s bedroom door and when he gave permission to enter, she peeked in to wish him good night. He wished her the same, and for a moment, he felt like her little boy again, before the hair and the girls, and the teenage angst. It was a good feeling, and she shut the door behind her happily before heading to the master bedroom. She took her time pampering herself and savouring the night. As she lotioned her hands, she took in the picture of Daniel, which eternally sat on her dresser.

“Perhaps, my love, I have finally found someone worthy enough to fill your shoes.” She said softly, and for the first time in all these long and lonely years, she felt like Daniel would be alright with her moving on. He would always have a place in her heart, but maybe there could be room for one more person there… a certain blonde haired beauty, perhaps, who kissed her like she was precious, and who could make her laugh without even trying.


End file.
